Reactions of Vinylidenecyclopropanes with Diphenyl Diselenide in the Presence of AIBN and Further Transformation To Produce New Naphthalene Derivatives

The reactions of vinylidencyclopropanes 1 with diphenyl diselenide 2 in the presence of AIBN produced the corresponding products 4 or 5 in moderate to good yields under mild conditions. The transformation of 4 to the corresponding methylenecyclopropanes 6 was achieved by treatment with hydrogen peroxide (H2O2) in toluene, and these were further transformed to the corresponding naphthalene derivatives 7 by treatment with 30 mol % of TfOH in dichloromethane.